Bromonitrin A
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| Category | Antibiotics |
| Catalog number | BBF-00182 |
| CAS | 23305-90-0 |
| Molecular Weight | 345.97 |
| Molecular Formula | C10H6Br2N2O2 |
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Description
Bromonitrin A is an antibiotic produced by Pseudomonas pyrrolnimica in a bromide-containing medium. It has anti-Gram-positive bacteria, Penicillium chrysogenum, Trichophyton interdigita and Candida albicans.
Specification
| IUPAC Name | 3-bromo-4-(3-bromo-2-nitrophenyl)-1H-pyrrole |
| Canonical SMILES | C1=CC(=C(C(=C1)Br)[N+](=O)[O-])C2=CNC=C2Br |
| InChI | InChI=1S/C10H6Br2N2O2/c11-8-3-1-2-6(10(8)14(15)16)7-4-13-5-9(7)12/h1-5,13H |
| InChI Key | QLBSUDRSMMIZHU-UHFFFAOYSA-N |
Properties
| Appearance | Yellow needle Crystal |
| Antibiotic Activity Spectrum | Gram-positive bacteria; fungi |
| Melting Point | 72-74°C |
| Solubility | Soluble in Chloroform, Methanol, water, acetone |
Reference Reading
1. Three-dimensional heterocycles: new uracil-based structures obtained by nucleophilic substitution at the sp2 carbon of bromoisoxazoline
Misal Giuseppe Memeo, Francesco Lapolla, Bruna Bovio, Paolo Quadrelli Molecules. 2014 Jun 24;19(6):8661-78. doi: 10.3390/molecules19068661.
The regioisomeric cycloadducts of bromonitrile oxide and N-benzoyl-2,3-oxaza-norborn-5-ene were easily prepared and elaborated into a novel class of uracil-based scaffolds. The key-synthetic step is the nucleophilic substitution at the sp2 carbon atom of the bromoisoxazoline three-dimensional heterocycles. The protocol to perform the nucleophilic substitution of uracil anions was optimized and adapted to the steric requirements of the substrates. A library of pyrimidine derivatives was prepared in very good yields and the products were fully characterized. They are proposed as nucleoside analogues and as synthons for β-turn motifs within PNA structures.
2. Hydride-induced anionic cyclization: an efficient method for the synthesis of 6-H-phenanthridines via a transition-metal-free process
Wei-Lin Chen, Chun-Yuan Chen, Yan-Fu Chen, Jen-Chieh Hsieh Org Lett. 2015 Mar 20;17(6):1613-6. doi: 10.1021/acs.orglett.5b00544. Epub 2015 Mar 12.
A novel procedure for hydride-induced anionic cyclization has been developed. It includes the reduction of a biaryl bromo-nitrile with a nucleophilic aromatic substitution (S(N)Ar). A range of polysubstituted 6-H-phenanthridines were so obtained in moderate to good yield with good substrate tolerance. This method involves a concise transition-metal-free process and was applied to synthesize natural alkaloids.
3. Synthesis of the precursors of iminosugars with 7-membered ring
Anna Osuch-Kwiatkowska, Sławomir Jarosz Carbohydr Res. 2022 Aug;518:108584. doi: 10.1016/j.carres.2022.108584. Epub 2022 May 18.
d-Glucose was converted into the orthogonally protected open-chain derivative having different blocks at both terminal positions: C1 and C6. Selective deprotection of the C1-position opened a route to intermediate with the D-gluco-configuration, while deprotection at the C6-position gave the L-gulo isomer. In both derivatives, the oxime functionality was installed at the proper terminal position, which produced the corresponding precursors of a family of 7-membered ring iminosugars. One of these oximes was converted into the direct precursor: 6,1-bromonitrile.
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Bio Calculators
* Our calculator is based on the following equation:
Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C1V1 = C2V2
* Total Molecular Weight:
g/mol
Tip: Chemical formula is case sensitive. C22H30N4O √ c22h30n40 ╳
